Studies of the microwave-assisted reaction of carbocyclic ketones with aniline

Studies of the microwave-assisted reaction of carbocyclic ketones with aniline Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2026, Volume: 75, Number: 3, Pages: 809-815 Pages count : 7 DOI: 10.1007/s11172-026-4935-0

Authors

Alykova E.A. ¹ , Sukhareva E.M. ¹ , Burko A.A. ¹ , Pichugin A.M. ¹ , Dyachenko V.S. ² , Savelev E.N. ¹ , Butov G.M. ² , Popov K.R. ¹ , Kustov L.M. ³ , Novakov I.A. ¹

Affiliations

1	Volgograd State Technical University, 28 prosp. imeni Lenina, 400005, Volgograd, Russian Federation
2	Volzhsky Polytechnic Institute (branch) of Volgograd State Technical University, 72 prosp. imeni Lenina, 404111, Volzhsky, Volgograd Region, Russian Federation
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The features of the microwave-assisted reaction of adamantan-2-one and camphor with aniline in the presence of anilinium chloride were studied. Formation of diphenylamine and products of its oxidative couplings was suppressed by performing the reaction under the inert atmosphere with microwave heating. Microwave irradiation accelerates the reaction rate by 1.5–2 times, increases the yield of the target products up to 60–78% and the reaction selectivity up to 99%. Evaluation of the effect of the reaction conditions on the product yield and product compositions indicated that the main products of the microwave-assisted synthesis carried out at a ratio of ketone: anilinium hydrochloride: aniline equal to 1: 0.5: 4 at 100 °C for 1 h are 2-(4-aminophenyl)tricyclo[3.3.1.13,7]decan-2-ol and 2-(4-aminophenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol. 4,4′-(Tricyclo[3.3.1.13,7]-decane-2,2-diyl)dianiline and 4,4′-(1,7,7-trimethylbicyclo[2.2.1]heptane-2,2-diyl)-dianiline were obtained in high yields by the reaction carried out at a molar ratio ketone: anilinium hydrochloride of 1: 2 at 150–180 °C for 12–20 h. Under the microwave synthesis conditions, camphor is less reactive than adamantan-2-one apparently due to the steric hindrance at the keto group.

Alykova E.A. , Sukhareva E.M. , Burko A.A. , Pichugin A.M. , Dyachenko V.S. , Savelev E.N. , Butov G.M. , Popov K.R. , Kustov L.M. , Novakov I.A.
Studies of the microwave-assisted reaction of carbocyclic ketones with aniline
Russian Chemical Bulletin. 2026. V.75. N3. P.809-815. DOI: 10.1007/s11172-026-4935-0 WOS Scopus OpenAlex

Submitted:	Oct 2, 2025
Published online:	Apr 25, 2026

≡ Web of science:	WOS:001748883400018
≡ Scopus:	2-s2.0-105037529906
≡ OpenAlex:	W7155631381